A m-quaterphenyl probe for absolute configurational assignments of primary and secondary amines

• Yuka Takeuchi,
• Mutsumi Kobayashi,
• Yuuka Gotoh,
• Mari Ikeda,
• Yoichi Habata,
• Tomohiko Shirai and
• Shunsuke Kuwahara

Beilstein J. Org. Chem. 2025, 21, 2211–2219, doi:10.3762/bjoc.21.168

• approximately 42 degree. The negative first and positive second Cotton effects in CD spectrum of (S)-2a indicates that the two long axes in the methoxybiphenyl chromophores constitute an M twist. The CD spectra of 1–ʟ-valinol conjugate (S)-2b exhibited the opposite sign for the Cotton effects compared with (S

Preparation of a furfural-derived enantioenriched vinyloxazoline building block and exploring its reactivity

• Madara Darzina,
• Anna Lielpetere and
• Aigars Jirgensons

Beilstein J. Org. Chem. 2025, 21, 1737–1741, doi:10.3762/bjoc.21.136

• amino alcohols derived from furfural and ʟ- or ᴅ-valinol were subjected to Torii-type ester electrosynthesis to obtain the corresponding unsaturated esters. These served as key intermediates to prepare (S)- and (R)-enantioenriched unsaturated amides by N-Alloc deprotection which induced concomitant

• reactions. Out of these, the aza-Diels–Alder reaction with TsNCO was successful, leading to a highly diastereoselective formation of an oxazolo[3,2-c]pyrimidine derivative. Keywords: aza-Diels–Alder reaction; electrosynthesis; furfural; valinol; vinyloxazoline; Introduction The utilization of biomass as

• trans-isomer of amide 5. Results and Discussion The protected furfuryl amino alcohols S-2d and R-2d were prepared by reductive amination of furfural (1) with ʟ- and ᴅ-valinol followed by N-protection with Alloc-Cl (Scheme 2). The amino alcohols S-2d and R-2d were then subjected to electrochemical

Architecture and synthesis of P,N-heterocyclic phosphine ligands

• Wisdom A. Munzeiwa,
• Bernard Omondi and
• Vincent O. Nyamori

Beilstein J. Org. Chem. 2020, 16, 362–383, doi:10.3762/bjoc.16.35

• was obtained by the reaction of ʟ-valinol with in situ-generated indolylacyl chloride. The latter compound was obtained through an oxalic acid-mediated chlorination of carboxylic acid 96 with dimethylformamide as catalyst in dichloromethane. Next, oxazoline derivative 98 was obtained via a

Quinone-catalyzed oxidative deformylation: synthesis of imines from amino alcohols

• Xinyun Liu,
• Johnny H. Phan,
• Benjamin J. Haugeberg,
• Shrikant S. Londhe and
• Michael D. Clift

Beilstein J. Org. Chem. 2017, 13, 2895–2901, doi:10.3762/bjoc.13.282

• % yield (Table 2, entry 10). Unfortunately, aliphatic 1,2-amino alcohols, such as valinol (1k), failed to undergo deformylation under the current conditions (Table 2, entry 11). Next, we investigated the use of various amine reaction partners 6 to access a variety of imine products 7 from phenylglycinol

New palladium–oxazoline complexes: Synthesis and evaluation of the optical properties and the catalytic power during the oxidation of textile dyes

• Rym Hassani,
• Mahjoub Jabli,
• Yakdhane Kacem,
• Jérôme Marrot,
• Damien Prim and
• Béchir Ben Hassine

Beilstein J. Org. Chem. 2015, 11, 1175–1186, doi:10.3762/bjoc.11.132

• amino acids). (S)-4-Isopropyl-2-(naphthalen-1-yl)oxazoline (2) was isolated in a moderate yield from the condensation of the L-valinol with naphthonitrile under microwave irradiation, while the second ligand 1,2-bis[(S)-4-phenyloxazoline]benzene (7) was synthesized from L-(α)-(+)-phenylglycinol under

• the same conditions of the reaction as described by B. Ben Hassine et al. [42]. The third ligand 3-[(4S)-4,5-dihydro-4-isopropyl-1,3-oxazol-2-yl]propanenitrile (11) was obtained using the reaction of 4-ethoxy-4-iminobutanenitrile monohydrochloride with L-valinol in high yield [43]. Synthesis of the

Total synthesis and cytotoxicity of the marine natural product malevamide D and a photoreactive analog

• Werner Telle,
• Gerhard Kelter,
• Heinz-Herbert Fiebig,
• Peter G. Jones and
• Thomas Lindel

Beilstein J. Org. Chem. 2014, 10, 316–322, doi:10.3762/bjoc.10.29

• valinol 4 (longest linear sequence). The optical rotation of the synthesized material ([α]D28 −37, c 0.09, MeOH) is a little smaller than reported for the isolated natural product ([α]D26 −55, c 0.10, MeOH) [1]. The 1H and 13C NMR spectra of 1 shows two sets of signals in a ratio of ca. 1:1. Clearly

Synthesis of axially chiral oxazoline–carbene ligands with an N-naphthyl framework and a study of their coordination with AuCl·SMe₂

• Feijun Wang,
• Shengke Li,
• Mingliang Qu,
• Mei-Xin Zhao,
• Lian-Jun Liu and
• Min Shi

Beilstein J. Org. Chem. 2012, 8, 726–731, doi:10.3762/bjoc.8.81

• were easily isolated by silica gel column chromatography in 37% yield and 44% yield, respectively. Similarly, using L-valinol, (Sa,S)-15b and (Ra,S)-15b could also be synthesized. Quaternization of the benzimidazole ring of (Sa,S)-15 and (Ra,S)-15 with R2I (R2 = Me, Et) gave the corresponding

Functionalization of heterocyclic compounds using polyfunctional magnesium and zinc reagents

• Paul Knochel,
• Matthias A. Schade,
• Sebastian Bernhardt,
• Georg Manolikakes,
• Albrecht Metzger,
• Fabian M. Piller,
• Christoph J. Rohbogner and
• Marc Mosrin

Beilstein J. Org. Chem. 2011, 7, 1261–1277, doi:10.3762/bjoc.7.147

• chloranil amidocuprate 87 undergoes an oxidative coupling providing the adenine derivative 88 in 71% yield. A treatment with D-valinol (89) affords the desired CDK inhibitor, purvalanol A (84) in 65% yield (Scheme 15) [44]. 2.2 The preparation of polyfunctional heterocyclic magnesium reagents by the